Solutions_Manual_for_Organic_Chemistry_6th_Ed 404

Solutions_Manual_for_Organic_Chemistry_6th_Ed 404 - 1 7-67...

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Unformatted text preview: 1 7-67 The intermediate anio�ss of hydroxide. axOH n forcesHtheOH lo H CH3 For simplicity, abbreviate I NHCH3 >1 R OHLi+ H /OH H H H OH �c c2 ffR a....-;c. R ___ Os:, R I I .o L/ H 'C:Y H H"S: H� plus presonance lus other � resonance forms forms tI Li· .0 I .0 \ .. + • r :· ---.- .0 I I �R plus resonance forms 1 7-68 OH equiv. OH lcquiI v. OH Cl-C(CH3h � C(CH3h NaOH CH3 _ � BHA, butyl.ted hydroxy.niso\c I AlCl3 Y3 OH OCH3 OCH hydroquinone plus other isomer OH OH 2 equiv. OH CH3I A Cl- C(CH3: (H3C)3C : c(CH3h BIrr, butyl.ted hydroxytoluenc I 6 AICI; Y AlCl3 ¢ • ¢1 .0 HH � ,C CH3 y � NHCH3 H . '"cH3CH,o - H- DJ'-R u� I H • CH3 V CH3 398 ...
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